Fatty-acid modified phenol-formaldehyde resins



Patented Mar. 24, 1953 FATTY-ACID MODIFIED PHENOL- FORMALDEHYDE. RESINSHerschel G. Smith, Wallingford, Troy L. Cantrell, Lansdowne, and Mark L.Hill, Boothwyn, Pa., assignors to Gulf Oil Corporation, Pittsburg Pa., acorporation of Pennsylvania No Drawing. Application July 8, 1949, SerialNo. 103,756

19 Claims.

This invention relates to new compositions of matter, and, moreSpecifically, it i concerned with compositions containing metallo saltsof phenol condensation products.

It is an object of this invention to provide new compositions of matterhaving advantageous physical and chemical properties and many valuableapplications. Other objects will appear from the following detaileddescription.

The objects of this invention are achieved by the provision of a newcomposition of matter comprising a higher fatty alcohol having at least8 carbon atoms and a metal salt of a condensation product of from 1 to 4mols of a mono-alkyl monohydric phenol having from 4 to 12 carbon atomsin the alkyl group, an equimolar amount of formaldehyde, and 1 mol of ahigher fatty acid having at least 8 carbon atoms.

These compositions are moderately hard thermoplastic materials ofstraw-yellow to dark brown color. In general, most of the compositionshave an indefinite melting point above about 170 F.; the melting pointbeing dependent on the particular metal of the metal salt and the amountof the higher fatty alcohol present. As stated, the compositions arethermoplastic and can be prepared in any suitable hardness ranging froma pliable mass at room temperature to a hardness comdcnsation product isconverted to a metal salt.

To the resulting metalsalt, a higher fatty alcohol of at least 8 carbonatoms is then added, yielding the composition of our invention.Alternatively, the higher fatty alcohol need not be added last,

but may be mixed with the ingredients used to form the condensationproduct, i. e., the phenol, formaldehyde and higher fatty acid. In otherwordsdthe higher fatty alcohol can be added during any stage of thismethod of preparnt on of our n w c mp itions.

It will be noted that the higher fatty alcohols of at least 8 carbonatoms and the higher fatty acids of at least 8 carbon atoms are, ineffect, hydrolysis products of fatty mono-esters having a total of atleast 16 carbon atoms. Also, it is known that the hydrolysis of esterswith a metal base, more commonly called saponification, results in theformation of a metal salt of the liberated fatty acids and free fattyalcohols. Accordingly, a preferred method of obtaining the compositionsof our invention comprises saponifying an ester having the formulawherein R is an aliphatic radical of at least 7 carbon atoms and R1 isan aliphatic radical of at least 8 carbon atoms, with a metal base andcondensing the saponification product with a mono-alkyl ,phenol andformaldehyde. This method avoids a separate neutralization step and theseparate addition of free fatty alcohols, two of the ingredients of ourcomposition being present originally in the form of an ester. In thecases where the metal of the salt to be prepared does not form a strongbase, e. g., the heavy metals, such as iron, copper, lead, etc., thesaponification is conducted with an alkali metal base, and after thecondensation product has been made, the alkali metal salt thereof issubjected to metathesis or double decomposition with a water solublesalt of such heavy metal, thereby obtaining the heavy metal salt of thecondensation product.

Anotherv alternative method of preparing our compositions involving theuse of an ester having the formula II R-C-ORi than the alkali metalsalts may be formed by metathesis.

While We do not know the exact chemical constitution of the condensationproduct, it is our present belief, without being limited thereto, thatone mol of the phenol is linked through a methylene group to the higherfatty acid or acid residue in the salt or ester, most probably at thealpha carbon atom of the fatty acid or acid residue. Any excess phenoland formaldehyde then condense onto the phenolic nucleus of the aboveproduct. In any event, we are certain that a unitary condensationproduct is obtained from the phenol, formaldehyde and fatty acid, i. e.,all of these ingredients are chemically combined. We are also certainthat the higher fatty acid reacts with the phenol and formaldehyde insuch manner as not to involve the carboxy group of the fatty acid, sincethe same type of product is finally obtained whether the phenol andformaldehyde are condensed with the free higher fatty acid, the fattyacid salts or the fatty acid esters.

Regardless of the specific method by which our compositions areprepared, the condensation and saponification reactions which are commonto all of the methods of preparation disclosed herein are conductedunder substantially identical conditions in each of the methods. Thecondensation reaction, which proceeds slowly at room temperature, isgenerally conducted at a mildly elevated temperature, say 150 to 175 F.,but not in excess of 250 F. The condensation reaction is conducted in aclosed vessel under reflux until all of the formaldehyde is consumed.Either acid or alkaline condensing agents may be employed as is known inthe art of phenol-formaldehyde condensations. After completion of thecondensation, the product is dehydrated by raising the temperature, sayto 280 F., to distill off all water. The same temperature conditions areemployed for the saponification and double decomposition reactions asare employed for the condensation; i. e., although these reactionsproceed at room temperature, it is preferred to speed up the reactionsby employing temperatures in the neighborhood of 150 to 175 F., but notin excess of 250 F.

As has been stated hereinabove, the proportions employed to prepare thecondensation product are 1 mol of the higher fatty acid or itsequivalent, 1 to 4 mols of the mono-alkyl phenol and l to 4 mols offormaldehyde. The phenol and formaldehyde are used in substantiallyequal amounts within the range of proportions stated. When amounts ofthe phenol and formaldehyde in excess of 1 mol are employed, the excesscondenses on to the phenolic nucleus of the condensation product of 1mol each of the higher fatty acid, the phenol and formaldehyde and formscondensation products of a greater consistency.

The free higher fatty alcohol in our composition functions as aplasticizer for the metal salt of the condensation product andfacilitates the formation of solutions of our composition in variouspetroleum solvents and mineral lubricating oils. Generally, in order toobtain the plasticizing and solubilizing functions of the free higherfatty alcohol, it is necessary to use it in amount 4 stantiallyequimolar (1 mol) amounts with the fatty acid.

The alkyl substituent of the mono-alkyl phenol employed in our inventionhas from 4 to 12 carbon atoms. The use of alkyl phenols having more orless carbon atoms in the alkyl group than the range stated is notsatisfactory because the resulting salts of the condensation productsprepared therefrom tend to be difiicultly soluble in mineral lubricatingoils. A. preferred grou of the mono-.alkyl phenols are those prepared byalkylating phenol with an olefin having from 4 to 12 carbon atoms in thepresence of a concentrated sulfuric acid catalyst at a temperature notexceeding 220 F. The resulting alkylated phenols may be washed withwater and dilute caustic soda to remove the sulfuric acid catalyst, butthis is not necessary. Other mono-alkyl phenols than the secondary andtertiary monoalkyl phenols obtained by alkylating phenol with an olefinhaving from 4 to 12 carbon atoms are also successfully employed. Thus,n-alkyl phenols having from 4 to 12 carbon atoms in the alkylsubstituent, prepared by alkylating phenol with an n-alkyl halide in thepresence of a Friedel- Crafts catalyst can also be employed.Representative mono-alkyl phenols include n-butyl phenol, sec-butylphenol, tert-butyl phenol, n-amyl phenol, sec-amyl phenol, tert-amylphenol, nhexyl phenol, n-octyl phenol, (alpha, alpha, gamma, gamma)tetramethylbutyl phenol, triisobutyl phenol and the like.

The higher fatty acids of at least 8 carbon atoms which are employed inpreparing the condensation products of our compositions are thesaturated and mono-olefinic aliphatic monocarboxylic acids. Theseinclude caprylic, pelargonic, nonylenic, capric, decylenic, undecylic,undecylenic, lauri-c, myristic, palmitic, stearic, oleic, ricinoleic,arachidic, behenic, erucic, brassidic, carnauba, cerotic, melissic andpsyllaic acids. Fatty acids of greater than mono-olefinic unsaturation,such as linoleic and linolenic acids, are undesirable since they tend toconfer undesirable hardening and drying properties on the condensationproducts made therefrom. Fatty acids having less than 8 carbon atoms arenot suitable since as the chain length decreases. the condensationproducts formed tend to become too hard and brittle and of decreasingsolubility in petroleum solvents.

The higher fatty alcohols of at least 8 carbon atoms which are employedas the solubilizing and plasticizing agent in our compositions are thesaturated and mono-olefinic aliphatic monohydri-c alcohols. Theseinclude n-octyl, 2-ethylhexyl, octenyl, nonyl, decyl, decenyl, undecyl,undecenyl, lauryl myristyl, cetyl, stearyl, oleyl, ricinoleyl, eicosyl,eicosenyl, docosyl, erucyl, ceryl and melissyl alcohols. Other fattyalcohols having less than 8 carbon atoms and polyolefinic fatty alcoholsare not satisfactory since they may evaporate too readily, have too higha flash point for safe use, or give an undesirable odor to the product.The lower alcohols are not good plasticizers, and the polyolefinicalcohols give undesirable hardening and drying effects.

As will be apparent from the foregoing, when that modification of theinvention which employs an ester of the formula (B being an aliphaticradical of at least '7 carbon atoms and R1 being an aliphatic radical ofat esters because of their relative cheapness.

least 8 carbon atoms) for the preparation of our composition is used,such ester is a combination of any of the foregoing alcohols and acids.Since many of such esters occur naturally, as in waxes, it is preferredto use such naturally occurring Examples of such materials are beeswax,carnauba Wax, candelilla wax, Chinese insect wax, cottonseed wax, flaxwax, ouricury wax, montan wax, sugar cane wax, sperm oil, spermaceti,sea weed wax, lanolin, and degras (wool fat). The use of degras isparticularly preferred. 7

Any meta1 can be employed for the production of the metal salts of thecondensation products disclosed herein. These include sodium, potassium,lithium, beryllium, calcium, magnesium, barium, strontium, zinc, silver,mercury, cadmium, aluminum, bismuth, tin, lead, copper, vanadium,antimony, chromium, manganese, iron, cobalt and nickel. In preparing ourcompositions by direct neutralization or by saponification of an ester,it is preferred to employ the alkali metal or alkaline earth metalhydroxides, because these are strong bases. Where salts of other metalsthan the alkali and alkaline earth metals .are to be prepared, it ispreferred to first make the alkali metal salt and then to make the saltof the other metal by metathesis with a water- The preparation of ournew compositions is illustrated by the following examples:

Example I Three thousand five hundred and twenty (3520) pounds of para(alpha,alpha,gamma,=- gamma) tetramethylbutyl phenol prepared byalkylating phenol with diisobutylene in the presence of a concentratedsulfuric acid catalyst were added to a reaction vessel equipped with areflux condenser and means for heating, cooling and agitating thecharge. The phenol added was the crude reaction product, stillcontaining the sulfuric acid catalyst. There was then added 3520 poundsof degras having a neutralization number between 40 and 60. The mixturewas agitated and heated to 160 F. Then 592 pounds of calcium hydroxidein a 33 per cent by weight water slurry were slowly added to thereaction vessel while maintaining the temperature at 160 F.

The temperature was held at this point while continuously agitating thereaction mass until the saponification of the degras was complete.Thereafter, 1360 lbs. of a 3'7 percent by weight aqueous solution ofform-aldehyde was slowly added to the reaction vessel while maintainingthe temperature not in excess of 170 F. After the formaldehyde wasadded, the mixture was refluxed at 170 F. until all the formaldehyde wasconsumed. Thereupon, the reflux condenser was replaced by an ordinarycondenser and the reaction mass was heated to 280 F. to distill off allwater and to dehydrate the product in the reaction vessel. The productin the reaction vessel was then filtered hot to remove excess calciumhydroxide and any other insolubles, The solidifled product was a fairlyhardlight'brown mass having a melting point of about 238 F.. It waspermanently thermoplastic and soluble in petroleum naphtha. The relativemolar proportions of the phenol, degras and formaldehyde in this examplewere in the ratio 2.7211237.

Example II Two hundred and six (206) pounds of para-(alpha,alpha,gamma,gamma) tetramethylbutyl phenol were mixed with 250pounds of degras and heated to 160 F. Then, while maintaining thistemperature, 50 pounds of sodium hydroxide dissolved in 128 pounds ofwater were slowly added with stirring. The mixture was held at thistemperature until saponiflcation of the degras was complete. Thereafter,82 pounds of a 37 per cent by weight aqueous solution of formaldehydewere slowly added to, the reaction mass and the temperature was notpermitted to exceed 170 F. The mixture was then refluxed until all ofthe formaldehyde was consumed. Thereafter, the mixture was heated to 380F. to distill off all water and the product in the reaction vessel wasfiltered hot to remove all insolubles. The solidified product was afairly hard light brown thermoplastic mass having a melting point ofabout 310 F. The relative molar proportions of the phenol, degras andformaldehyde in this example were in the ratio 2.2:l:2.2.

Typical properties of the degras used in the above examples are:

Specific gravity 60/ 60 F 09322-09449 Solidification point, F. -104Saponification No. 84-127 Iodine No. 15-215 Example III Ninety (90)pounds of the product of Example II was subjected to a doubledecomposition reac tion with 63 pounds of ferrous chloride dissolved inwater by agitating the reactants at temperatures of -170 F. The reactionproduct was washed with water to remove water soluble salts and thendried at 250 F. The resulting iron salt composition was a thermoplasticsolid having an indefinite melting point in excess of 180 F.

Example I V The barium salt composition was prepared in the same manneras the iron salt of Example III by reacting 90 pounds of the product ofExample II with 35 pounds of barium chloride dissolved in water. Theresulting barium salt composition was a thermoplastic solid having anindefinite melting point in excess of 240 F.

Example V In a similar manner, the stannous salt, the aluminum salt andthe cupric salt were prepared by reacting in each instance 90 pounds ofthe product of Example II with 39 pounds of stannous chloride dissolvedin water for the stannous salt, 23 pounds of aluminum sulfate dissolvedin water for the aluminum salt and 14 pounds of cupric chloridedissolved in water for the copper salt. Each of the resulting salts hadan indefinite melting point in excess of about 212 F. but they werethermoplastic solids at room temperature.

It should be noted that although the product of Example II had a meltingpoint of 310 K, it was slightly soluble and/or sufficiently dispersiblein water to permit the double decomposition reactions of Example III, IVor V. In lieu of replacing all of the sodium ion in the doubledecomposition reactions, if desired, any portion thereof may be replacedby controlling the amount of the water-soluble salt added, therebyforming mixed salts.

with 1 mol of oleic acid and heated to F. Then 1 mol of formaldehydewasslowly; added enamels 'at a temperature not in excess of 165 F. Themixture was then refluxed until all of the formal dehyde was consumed.Thereafter, 1 mol of sodium hydroxide in 3 parts of water was added toneutralize the mixture. To the neutralized mixture there was then added0.5 mol of cetyl alcohol. The mixture was agitated while heating to 385F. to distill off all water. The product was then filtered hot to removeany insolubles. The solidified product was a fairly hard light brownmass having a melting point of about 255 )5.

Our new compositions have many advantageous uses. Since the compositionshave positive anti-corrosive properties, they are eminently useful inpreparing slushing compounds, as undercoatings in the lagging ofmetallic vessels and as anti-corrosive additives in mineral oillubricant compositions. When used as protective coatings for metals, thecompositions of our invention form tough, adherent, water-repellentfilms; yet when it is desired to remove the coatings, they may be easilyremoved merely by wiping with a cloth dipped in kerosene, gasoline,Stoddard solvent or other petroleum naphtha. The compositions formexcellent textile impregnants when dissolved in a volatile petroleumnaphtha, since they make the textiles water-repellent and preventrotting of the textile base. When added to paints, our compositionspromote adhesion and prevent scaling, rusting and other corrosion ofmetal parts I covered by the paint film. In coating composi 'tionshaving an asphalt base, small amounts of our compositions act asanti-oxidant and modifier which eliminates or materially reducescracking, checking, alligatoring and slipping. Our compositions act aseffective adhesives in insecticidal compositions employing residualtoxicants, such as p-p, bis(chlorophenyl) 1,1,1-trichloroethane,tetraethylpyrophosphate, benzene hexachloride,12,4,5,6}?,8,8-octachlor-4,7-methano-3a,4,7,Va-tetrahydroindane, etc.Our new compositions also modify the structure of both amorphous andcrystalline parafiin waxes. Our new compositions are also useful inmodifying vegetable, animal or mineral wax compositions to give improvedcharacteristics to floor coverings, metal coverings, furniture polishesand automobile polishes. In wax polishes, the compositions of ourinvention can replace the usual beeswax plasticizer and modifier, oreven hard waxes like carnauba wax. solvent has evaporated from themodified wax polish, there remains a clear, hard, plastic film.

The following examples are illus ative of some of the uses of ourcompositions.

Example VII A residual insecticide spray was prepared to contain 6 percent by weight of p-p',bis (chlorophenyl)-1,1,1-trichlorethane in aninsecticide naphtha base. A comparison was made between this spray andan identical spray containing additionally 1 per cent by weight of theproduct of Example I, as follows: The two insecticide compositions weresprayed on a panel in an amount of 1 ounce of liquid per 100 sq. ft. andallowed to dry. The panel was then placed in such manner as to becontacted with flies (1M usca domestica). The apparent effective time ofkilling of the spray not containing our composition was 94 days; whereasthe apparent effective time of killing of the spray containing ourcomposition wa more than 165 days.

Example VIII A polishing wax was prepared by substituting When thepetroleum 8 the product ofExample I for :ei-ther camauba wax .or beeswaxina standard wax. A compar- Liquid at room temperature.

Polish A, which was the standard, presented the conventional car waxappearance and polished to a film having a smooth hard finish. Polish B,in which the beeswax was replaced by the composition of our invention,was softer than the standard and also polished to a film having a smoothhard finish. Polish B, in which half of the carnauba wax was replaced bythe composition of our invention, was a mush-like material easilyapplied to leave a smooth hard finsh. Polish C in which all the carnaubawax was replaced by the composition of our invention, was liquid at roomtemperature and left a smooth hard film. The compositions of ourinvention may thus be used to vary the characteristics of wax polishes,making them easier to apply and easier to rub into a smooth hard coatwhich is more plastic and more impervious to water than conventional waxcoats. The film prepared from waxes containing the compositions of ourinvention have better nonslip properties than a film of a standardcarnauba base wax. The waxes containing the compositions of ourinvention are also cheaper than standard carnauba base waxes, since theexpensive carnauba wax can be replaced wholly or in part with outinexpensive compositions.

Example IX A canvas cover was treated with a 10 per cent by weightsolution in V. M. & P. naphtha of the copper salt composition of ExampleV. The canvas was then exposed to weather. After six months, the canvaswas still resistant to water and showed no evidence of rotting where itcame in contact with brackish water.

Example X A canvas boat cover was treated with a 10 per cent solution inV. M. & P. naphtha of the aluminum salt composition of Example V. Abrush was used to apply the solution to the cover. After six monthsweathering, the canvas was impervious to water and showed nodeterioration.

Resort may be had to such modifications and variations as fall withinthe spirit of the invention and the scope of the appended claims.

We claim:

1. A composition of matter comprising a higher fatty alcohol selectedfrom the class consisting of the saturated and mono-olefinic aliphaticmonohydric alcohols having at least 8 carbon atoms and a metal salt of acondensation product of from 1 to 4 mols of a mono-alkyl monohy-dricphenol having from 4 to 12 carbon atoms in the alkyl group, an equimolaramount of formaldehyde, and 1 mol of a higher 9 fatty acid selected fromthe class consisting of the saturated and mono-olefinic aliphaticmonocarboxylic acids having at least 8 carbon atoms, the amount of saidhigher fatty alcohol ranging from to 2 mols per mol of said higher fattyacid.

'2. The composition of claim 1, wherein the higher fatty alcohol isdegras fatty alcohols, and the higher fatty acid is degras fatty acids.

3. The composition of claim 1, wherein the higher fatty alcohol is spermoil fatty alcohols, and the higher fatty acid is sperm oil fatty acids.

4. The composition of claim 1, wherein the higher fatty alcohol isbeeswax fatty alcohols and the high-er fatty acid is beeswax fattyacids.

5. The composition of claim 1, wherein the metal salt is an alkali metalsalt.

6. The composition of claim 1, wherein metal salt is an alkaline earthmetal salt.

'7. The composition of claim 1, wherein metal salt is a calcium salt.

8. The composition of claim 1, wherein metal salt is a sodium salt.

9. The composition of claim 1, wherein metal salt is a copper salt.

10. A composition of matter comprising degras fatty alcohols and 'acalcium salt of a condensation product of from 1 to 4 mols of (alpha,alpha, gamma, gamma) tetramethylbutyl phenol, an equimolar amount offormaldehyde and 1 mol of degiras fatty acids, the amount of said degrasfatty alcohols ranging from A; to 2 mols per mol of said degras fattyacids.

11. A composition of matter comprising cetyl alcohol and a sodium saltof a condensation product of from 1 to 4 mols of tertiarybutyl phenol,an equimolar amount of formaldehyde and 1 mol of oleic acid, the amountof cetyl alcohol ranging from A; to 2 mols per mol of oleic acid.

12. The process which comprises condensing from 1 to 4 mols of amono-alkyl monohydric phenol having from 4 to 12 carbon atoms in thealkyl group, an equimolar amount of formaldehyde and 1 mol of a higherfatty acid selected from the class consisting of the saturated andm-ono-olefinic aliphatic monocarboxylic acids having at least 8 carbonatoms, then forming a metal salt of the condensation product, and addingin an amount of from A; to 2 mols per mol of said higher fatty acid ahigher fatty alcohol selected from the class consisting of the saturatedand mono-olefinic aliphatic monohyd ric alcohols having at least 8carbon atoms.

13. The process which comprises condensing from 1 to 4 mols of amono-alkyl monohydric phenol having from 4 to 12 carbon atoms in thealkyl group, an equimolar amount of formaldehyde and 1 mol of an esterhaving the formula the the

the

the

wherein R is an aliphatic radical of at least 7 carbon atoms and R1 isan aliphatic radical of at least 8 carbon atoms, both R and R1 beingselected from the class consisting of saturated and monoolefinicaliphatic radicals, and saponifying the condensation product with a 10strong base selected from the class consisting of alkali metal andalkaline earth metal hydroxides.

14. The process which comprises saponifying 1 mol of an ester having theformula wherein R is an aliphatic radical of at least '7 carbon atomsand R1 is an aliphatic radical of at least 8 carbon atoms, both R and R1bein selected from the class consisting of saturated and mono-olefinicaliphatic radicals, with a strong base selected from the classconsisting of alkali metal and alkaline earth metal hydroxides, andreacting the saponified mixture with 1 to 4 mols of a mono-alkylmonohydric phenol having from 4 to 12 carbon atoms in the alkyl groupand an equimolar amount of formaldehyde to condense together the metalsalt of the fatty acid derived from the saponification, the phenol andthe form-aldehyde.

15. The process of claim 14, wherein the base is an alkali metalhydroxide, and salts of other metals are prepared by metathesis of thealkali metal salt of the condensation product with a water-soluble saltof such other metal.

16. The process which comprises saponifying 1 mol of degras with calciumhydroxide, and reacting the saponified mixture with 1 to 4 mols of(alpha, alpha, gamma, gamma) tetramethylbutyl phenol and an equimolaramount of formaldehyde to condense together the calcium salt oftheidegras fatty acids, the phenol and the formaldehyde.

1'7. The process which comprises sa/ponifying 1 mol of degras withsodium hydroxide, and reacting the saponified mixture with 1 to 4 molsof (alpha, alpha, gamma, gamma) tetramethylbutyl phenol and an equimolaramount of formaldehyde to condense together the sodium salt of thedegras fatty acids, the phenol and the formaldehyde.

18. The process of claim 17, wherein other metal salts of thecondensation product are prepared by metathesis of the sodium salt ofthe condensation product wit-h a water-soluble salt of such other metal.

19. The process of claim 18 wherein the watersoluble salt is awater-soluble copper salt.

HERSCHEL G. SMITH.

TROY L. CANTRELL.

MARK L. I-HLL.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Number Name Date 2,152,633 Catlow et al. Apr. 4,1939 2,506,904 Smith et al. May 9, 1950 FOREIGN PATENTS Number CountryDate 327,713 Great Britain Mar. 31, 1930 556,395 Germany July 21, 1932

1. A COMPOSITION OF MATTER COMPRISING A HIGHER FATTY ALCOHOL SELECTEDFROM THE CLASS CONSISTING OF THE SATURATED AND MONO-OLEFINIC ALIPHATICMONOHYDRIC ALCOHOLS HAVING AT LEAST 8 CARBON ATOMS AND A METAL SALT OF ACONDENSATION PRODUCT OF FROM 1 TO 4 MOLS OF A MONO-ALKYL MONOHYDRICPHENOL HAVING FROM 4 TO 12 CARBON ATOMS IN THE ALKYL GROUP, AN EQUIMOLARAMOUNT OF FORMALDEHYDE, AND 1 MOL OF A HIGHER FATTY ACID SELECTED FROMTHE CLASS CONSISTING OF THE SATURATED AND MONO-OLEFINIC ALIPHATICMONOCARBOXYLIC ACIDS HAVING AT LEAST 8 CARBON ATOMS, THE AMOUNT OF SAIDHIGHER FATTY ALCHOL RANGING FROM 1/8 TO 2 MOLS PER MOL OF SAID HIGHERFATTY ACID.